| Revision as of 19:47, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit |
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{{hatnote group| |
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{{Distinguish|text = the mercurial diuretic ]}} |
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{{for|the DC comics Movie Universe|DC Extended Universe}} |
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{{chembox |
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{{chembox |
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| ImageFile = Diuron.svg |
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| verifiedrevid = 431585859 |
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| ImageAlt = Skeletal formula of DCMU |
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| ImageFile = Diuron.png |
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| ImageFile1 = DCMU-3D-balls.png |
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| OtherNames = 3-(3,4-dichlorophenyl)-1,1-dimethylurea |
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| ImageAlt1 = Ball-and-stick model of the DCMU molecule |
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| PIN = ''N''′-(3,4-Dichlorophenyl)-''N'',''N''-dimethylurea |
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| OtherNames = 3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 3008 |
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| ChemSpiderID = 3008 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) |
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| ChEBI = 116509 |
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| ChEBI = 116509 |
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| SMILES = Clc1ccc(NC(=O)N(C)C)cc1Cl |
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| SMILES = Clc1ccc(NC(=O)N(C)C)cc1Cl |
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| InChIKey = XMTQQYYKAHVGBJ-UHFFFAOYAZ |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 278489 |
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| ChEMBL = 278489 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C18428 |
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| KEGG = C18428 |
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| PubChem = 3120 |
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| EC_number = 206-354-4 |
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| RTECS = YS8925000 |
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| UNNumber = 3077, 2767 |
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| UNII = 9I3SDS92WY |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>9</sub>H<sub>10</sub>Cl<sub>2</sub>N<sub>2</sub>O |
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| C=9|H=10|Cl=2|N=2|O=1 |
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| MolarMass = 233.10 g/mol |
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| Density = 1.48 g/cm<sup>3</sup> |
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| Density = 1.48 g/cm<sup>3</sup> |
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| MeltingPt = 158 °C |
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| MeltingPtC = 158 |
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| BoilingPt = 180 °C |
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| BoilingPtC = 180 |
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| Solubility = 42 mg/L |
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| Solubility = 42 mg/L |
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| Appearance = white crystalline solid<ref name=PGCH/> |
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| VaporPressure = 0.000000002 mmHg (20°C)<ref name=PGCH/> |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| PEL = none<ref name=PGCH>{{PGCH|0247}}</ref> |
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| EUClass = Harmful ('''Xn'''); Dangerous for the environment ('''N''') |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> |
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| FlashPt = noncombustible |
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| FlashPt_ref =<ref name=PGCH/> |
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| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|351|373|410}} |
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| PPhrases = {{P-phrases|201|202|260|264|270|273|281|301+312|308+313|314|330|391|405|501}} |
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'''DCMU''' ('''3-(3,4-dichlorophenyl)-1,1-dimethylurea''') is a ] that inhibits ]. It was released by ] in 1954 under the trade name of '''Diuron'''. |
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'''DCMU''' ('''3-(3,4-dichlorophenyl)-1,1-dimethylurea''') is an ] and ] of the aryl ] class that inhibits ]. It was introduced by ] in 1954 under the trade name of '''Diuron'''. |
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==History== |
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In 1952, chemists at ] patented a series of ] ] derivatives as ]. Several compounds covered by this patent were commercialized as herbicides: ] (3-chloro-4-methylphenyl) and DCMU, the (3,4-dichlorophenyl) example.<ref name=Todd>{{cite patent |country=US |number=2655445 |status=patent |gdate=1953-10-13 |fdate=1952-02-14 |pridate=1949-12-06 |invent1 =Todd C.W. |title=3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |assign1=E. I. du Pont de Nemours & Co.}}</ref><ref name=Liu>{{cite book |doi=10.1016/B978-0-12-374367-1.00080-X |chapter=Phenylurea Herbicides |title=Hayes' Handbook of Pesticide Toxicology |year=2010 |last1=Liu |first1=Jing |pages=1725–1731 |isbn=9780123743671 }}</ref> Subsequently, over thirty related urea ] with the same mechanism of action reached the market worldwide.<ref>{{cite web |url=http://www.alanwood.net/pesticides/class_herbicides.html#urea_herbicides |title=Urea herbicides |website=alanwood.net|access-date=2021-03-26}}</ref> |
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==Synthesis== |
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As described in the du Pont patent, the starting material is 3,4-dichloro], which is treated with ] to form a ] derivative. This is subsequently reacted with ] to give the final product.<ref name=Todd /> |
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:Aryl-NH<sub>2</sub> + COCl<sub>2</sub> → Aryl-NCO |
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:Aryl-NCO + NH(CH<sub>3</sub>)<sub>2</sub> → Aryl-NHCON(CH<sub>3</sub>)<sub>2</sub> |
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==Mechanism of action== |
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==Mechanism of action== |
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DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the ] binding site of ] II, disallowing the electron flow from where it is generated, in photosystem II, to plastoquinone<ref>1</ref>. This interrupts the photosynthetic ] in photosynthesis and thus blocks the ability of the plant to turn light energy into chemical energy (] and ]). |
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DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the Q<sub>B</sub> ] binding site of ], disallowing the electron flow from photosystem II to plastoquinone.<ref>{{Cite journal | doi = 10.1016/0014-5793(86)80911-5 | title = Evidence for a dual function of the herbicide-binding D1 protein in photosystem II | year = 1986 | last1 = Metz | first1 = J | last2 = Pakrasi | first2 = H | last3 = Seibert | first3 = M | last4 = Arntzer | first4 = C | journal = FEBS Letters | volume = 205 | issue = 2 | pages = 269| s2cid = 84205263 | doi-access = free }}</ref> This interrupts the photosynthetic ] in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (] and ]). |
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DCMU only blocks electron flow from photosystem II, it has no effect on photosystem I or other reactions in photosynthesis, such as light absorption or carbon fixation in the ]. |
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DCMU only blocks electron flow from photosystem II, it has no effect on photosystem I or other reactions in photosynthesis, such as light absorption or carbon fixation in the ].{{Citation needed|reason=reliable source needed for the whole sentence|date=April 2014}} |
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However, because it absorbs electrons ] from water in ], the electron "hole" of ] cannot be satisfied, effectively shutting down photosynthesis by blocking the reduction of NADP<sup>+</sup> to NADPH, and the cyclic photosynthetic pathway since electron shuttling is associated with proton pumping across the membrane into the ]. |
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However, because it blocks electrons produced from water oxidation in ] from entering the plastoquinone pool, "linear" photosynthesis is effectively shut down, as there are no available electrons to exit the photosynthetic electron flow cycle for reduction of ] to NADPH. |
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In fact, it was found that DCMU not only does not inhibit the ], but, under certain circumstances, actually stimulates it.<ref>HUBER, S.C. EDWARDS, G.E. (1976), Studies on the Pathway of Cyclic Electron Flow in Mesophyll Chloroplasts of a C4 Plant, Biochimica et Biophysica Acta (BBA) - Bioenergetics, Volume 449, Issue 3, 6 December 1976, Pages 420-433, {{doi|10.1016/0005-2728(76)90153-5}}</ref><ref>{{cite journal | pmc = 1056483 | pmid=16665372 | volume=83 | issue=4 | title=Regulation of Cyclic Photophosphorylation during Ferredoxin-Mediated Electron Transport : Effect of DCMU and the NADPH/NADP Ratio |date=April 1987 | journal=Plant Physiol. | pages=965–9 | doi=10.1104/pp.83.4.965| last1=Hosler | first1=J. P. | last2=Yocum | first2=C. F. }}</ref> |
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Because of these effects, DCMU is often used to study energy flow in ]. |
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==Applications== |
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Besides its use as a herbicide, DCMU is often used to research energy flow in ]. |
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==Toxicity== |
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DCMU (Diuron) has been characterized as a known/likely human carcinogen based on animal testing.<ref>{{cite web |title=Diuron |url=https://pubchem.ncbi.nlm.nih.gov/source/hsdb/382 |website=National Center for Biotechnology Information |publisher=United States National Library of Medicine |number=382 |access-date=9 November 2021}}</ref><ref>{{cite tech report |type=Memorandum |first1=Taylor |last1=Linda |first2=Rinde |last2=Esther |title=Carcinogenicity Peer Review of Diuron |number=20460 |institution=United States Environmental Protection Agency |date=1997-05-08 |url=https://www3.epa.gov/pesticides/chem_search/cleared_reviews/csr_PC-035505_8-May-97_042.pdf |format=PDF |place=Washington, D.C.}}</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}}<!--added under references heading by script-assisted edit--> |
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* ''FEBS Letters'' (1986) '''205''', 269-274 |
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{{Herbicides}} |
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{{Herbicides}} |
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